Stop should-ing yourself
Self-criticism gets you nowhere
Hey there —
How many “shoulds” are on your to-do list today?
🤔 I should clean out that closet.
😬 I should write that video outline. (In fact, I should have done it yesterday.)
😥 I should be more productive.
😫 I should be further along.
We all do it. Every day, from simple to-dos to who or where we are, we weigh ourselves down under a pile of shoulds.
And as the day (or our life) progresses and we don’t accomplish these guilt-laden goals, we feel more and more defeated, frustrated, and cranky.
But what if — and hear us out — you stopped should-ing yourself?

Of course, for something that sounds so simple, this can be a monumental task.
“Should” is ingrained in our vocabulary — it pops into our heads and rolls off our tongues with more practiced speed than our daily coffee order.
But when was the last time should-ing yourself actually motivated you to do…anything? (We’re guessing the answer is never — or at least, not in a healthy way).
That’s because the word “should” is full of expectations — from ourselves, others, and the culture around us — and often comes with a side of shame and regret. And ironically, it actually makes it harder for you to do the thing you’re telling yourself you “should” be doing.
As Psychologist Dr. Sophie Mort describes it, shoulds are an active form of self-criticism. And that criticism creates anxiety and stress, triggering our desire to procrastinate and making it more likely that we’ll fall back into bad habits or patterns of behavior.
“There is nothing wrong with having a goal if it's based on something you genuinely want for yourself. However, when we ‘should’ ourselves we undermine ourselves from the start. Instead of starting from a place of strength, comfort and empowerment (which almost certainly produces the best outcomes) we start from a place of less-than, a place of not good enough...insecurity doesn’t motivate people in a sustainable way.”
Not only is it far from motivational, but the broad concept of “should” is an illusion. If you should be further along, or better, or faster, you’re implying there’s a single pace or path to success and clearly you’re not on it. And that simply isn’t true! Life is full of ups, downs, and the unexpected, and we’re all on our own unique journey.
One solution Dr. Mort suggests (along with questioning why you think you should and if it really aligns with your values and beliefs), is to flip the script and replace “I should” with “I could” or “I would like to.”
Another great flip? Instead of berating yourself for a perceived failure, reframe “I should have” with a follow up: “I could have finished that design project yesterday, but I also needed to give my mind a break in order to do my best work.”
Affirming who you want to be, where you want to go, and the steps you’re taking to get there is way more motivational than beating yourself up.
So the next time you’re tempted to should yourself — just say “no” to self-criticism. Instead, turn the tables and trade that pressure-filled word for some positive self-empowerment. 🌟


How to deal with regret
by Jelena Kecmanovic
Whether it’s something we think we “should” have done, or something we wish we hadn’t, regret is a universal human experience. And with rising levels of perfectionism and information overload, more people are dealing with the self-blame and dissatisfaction that comes with it.
If that’s you, psychologist Jelena Kecmanovic offers a step-by-step guide on how to feel, forgive, and reframe your current regrets (and reduce future ones).
The best part? These strategies won’t just help you cope with your regrets — they’ll help you turn them into a positive force in your life. 💫

They can’t all be hits
by Caroline Cala Donofrio
In this reflection on writing, marketing, and the dreams we aspire to, author Caroline Cala Donofrio offers a simple phrase that might help ease the pressure that so often stifles our creativity: “They can’t all be hits.”
“A ‘hit,’ after all, is a very narrow definition of success—critically acclaimed and commercially successful. And sure, that sounds like a dream. But trying to reverse engineer one is like trying to make a meteor shower or a thunderstorm or any other awe-inspiring natural occurrence—really not our business.”

Give less f*cks
By @nicole_coenen
Here’s a quick reminder from your friendly neighborhood lumberjack: you don’t have to give your f*cks to just anything.
In fact, when you save ‘em for the important stuff, the f*cks you do give will really matter.


QUESTION
What financial habits have helped you to strike the right balance between spending adequately to meet your needs and saving for a comfortable lifestyle and emergencies?
— Durga M., India
ANSWER
First, we’d say resist the urge to “should” yourself about your finances. Instead, this is a great place to apply that “I would like to…” reframing. What are your financial priorities (paying off debt, buying a home, being able to travel, etc.)? What does a “comfortable lifestyle” look like for you?
Then, as you work toward these personal goals, you can use the strategies and percentages most experts agree on as a starting point for balancing spending vs. saving:
Save a $1,000 emergency fund, then once all your debts are paid (🎉) increase that to 3-6 months’ worth of expenses.
Work toward dedicating at least 20% of your paycheck toward debt or savings.
When it comes to habits that will help you reach these goals, here’s one to build and one to break:
🛠️ Build: Consistent saving. Decide what percentage of your income you’re going to save and stick with it, even if you start making more money. (You might even automate this habit by having it automatically deducted from your paycheck or transferred from your checking to savings account each month.) This will help you avoid “lifestyle creep” — aka, increasing your spending every time you get a raise (which can keep you stuck in a cycle of living paycheck to paycheck).
☠️ Break: Buying stuff you don’t need. Before you hit purchase, ask yourself if whatever you’re buying aligns with your values and your financial goals — and whether it’s really going to contribute to your long-term happiness, contentment, and your most meaningful life.
Tap the link to dive deeper into these topics and to hear some more essential finance tips from Matt!
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Written by Ashley Martin
Edited by Matt D'Avella